Softening agent for cotton and for synthetic textile substrates



United States Patent 3,509,048 SOFIENING AGENT FOR COTTON AND FOR SYNTHETIC TEXTILE SUBSTRATES James Marvin Brown, Charlotte, N.C., assignor to American Cyanamid Company, Stamford, Conn., a corporation of Maine No Drawing. Filed Oct. 3, 1966, Ser. No. 583,976 Int. Cl. D06m 13/32, 13/26 US. Cl. 252-857 1 Claim ABSTRACT OF THE DISCLOSURE A softening agent for cotton and other cellulosic textiles comprising a sulfated mono-oleate ester of diethylene glycol. Textiles treated with this softening agent are characterized by good rewettability and the agent is elTective on textiles in the presence of metallic ions.

This invention relates to a novel process for producing a novel composition of a class normally employed as softening agents for cotton and other cellulosic textiles. More particularly, the invention relates to the alkali metal salts of sulfated mono-olefinate esters of diethylene glycol.

Heretofore, a major problem encountered in the employment of textile softeners for cellulosic fabrics has been the lack of stability of the softener composition to metallic ions While concurrently retaining the properties of good rewettability and softening. For example, as a result of this prior poor stability of various softening agents, it has not been possible to use a finishing softener for cellulosic fabrics previously resin-treated.

As a typical example of the lack of stability of some of the prior softening compositions, when a prior composition is placed at about 6% by weight in an aqueous solution containing about 1% of sodium bisulfite and not more than about 1% magnesium chloride, such a test indicates that the higher percentages of sulfated fatty-acid sodium salt cause the softening composition to be much less suitable for obtaining a good and desirable textile finish, whereas when the sulfated fatty-acid sodium salt is employed in smaller percentages, a marked lack of stability of the softening composition results.

Accordingly, it is an object of this invention to produce a softening composition suitable for the treatment of cellulosic textiles.

Another object is to produce a softening composition stable to metallic ions and characterized by the properties of good rewettability and softening.

Another object is to obtain a cellulosic fabric impregnated wtih the above composition.

Another object is to obtain a process for the production of the above cellulosic composition.

Other objects become apparent from the above and following disclosure.

The objects of this invention are obtained by the employment of an alkali salt of sulfated mono-olefinate ester of a polyalkylene polyhydroxy-alcohol-type compound. The preferred alkali metal is sodium, the preferred olefinate ester is of oleic acid, and the polyalkylene polyhydroxy-alcohol-type compound preferred for the invention is diethylene glycol.

The alkali salt of the sulfated mono-olefinate ester of a diethylene glycol-type compound is employed in a conventional manner to impregnate a cellulosic textile material such as cotton to obtain the novel impregnated cellulosic material of this invention.

The alkali salt of sulfated mono-olefinate ester of a diethylene glycol-type compound is formed by a process comprising (1) reacting an olefinic acid with diethylene "ice glycol-type compound sufiiciently to form substantially a major amount of mono-olefinate ester of polyalkylene polyhydroxy-alcohol-type compound, (2) sulfating said ester comprising reacting said ester with fuming sulfuric acid sufliciently to form substantially a major amount of sulfated mono-olefinate ester of polyalkylene polyhydroxyalcohol-type compound, and (3) reacting (a) said sulfated mono-olefinate ester of polyalkylene polyhydroxyalcohol-type compound with (b) an alkali metal hydroxide sufficiently to form the alkali metal salt of said ester.

The advantages made possible by the softening composition of this invention is a combination of advantages heretofore not possible with softeners of the prior art. By the employment of the invention as described above, it is possible to obtain a stable finish and to concurrently obtain a treated textile cellulosic material such as a textile fiber or fabric thereof which is characterized by a desirable softness of hand and the property of good rewettability. The advantages of this invention are particularly applicable to materials such as denim and toweling.

The polyalkylene polyhydroxy-alcohol-type compound of this invention may be derived from any of the olefine acids typically represented by the formula C H COOH, such as acrylic acid, butenic acid, pentenic acid, hexenic acid, teracrylic acid, hypogaeic acid, oleic acid, erucic acid, and the like.

The ester-portion of the polyalkylene polyhydroxyalcohol-type compound of this invention refers to the ester of any polyalkylene glycol which ester is water soluble and which polyalkylene glycol is derived from alkylene oxides or glycols, such as those typically represented by the formula HO(C,, H O) H, in which n is an integer from 2 to about 8 and in which n is an integer from about 15 to about 450. It is not necessary that all the alkylene radicals present necessarily be the same; i.e., polyglycols containing a mixture of alkylene radicals can be used, including ethylene, propylene, trimethylene, tetramethylene, and the like radicals.

Although it should be noted that it is critical to this invention that the olefinate ester be a monoolefinate, as contrasted to a di-olefinate ester, it is within the scope of this invention to employ the functionally equivalent derivatives of olefinic acid, and of a polyalkylene poly hydroxy-alcohol-type compound, provided that the advantages of this invention are not negated by the employment of such a derivative.

The application of the novel product or composition of the product of this invention to a cellulosic material such as a textile fabric is carried out by any standard or conventional processing technique, such as dipping, exhaustion, padding, spraying, and the like. Although water is a conventional solvent normally employed in the application of the composition of this invention to a cellulosic material, such as a textile fabric, it is within the scope of the invention also to employ alone or in a compatiable mixture, any one or more solvents such as acetone, dimethyl formamide, benzene, tetrahydrofuran, toluene, xylene, and the like; but it is also contemplated that emulsions may be employed. The chlorinated hydrocarbons such as ethylene dichloride, tetrachloroethane, and carbon tetrachloride are other typical examples of a suitable vehicle. In order to obtain the benefits of this invention for a cellulosic material impregnated with the softener of this invention, it is necessary only that the material be impregnated sufficiently to obtain the desired properties described above. However, normally it is necessary that the alkali salt of sulfated mono-olefinate ester of a polyalkylene polyhydroxy-alcohol-type compound be employed in an amount suflicient to obtain from about 0.25% up to about 2% solids on the weight of the fabric (material) after drying. However, it should be noted illustrating the invention and does not limit the invention except insofar as the invention is limited and the appended claims.

Example To a glass-lined reactor charge 3626 lbs. diethylene glycol, 9675 lbs. oleic acid and 11 lbs. para-toluenesulfonic acid.

Heat batch to a maximum temperature of 185 C. allowing temperature to rise as reaction proceeds. Apply vacuum as water-of-reaction distillation rate slackens.

React under vacuum to an acid number of 11 maximum.

Vent vacuum with inert gas and cool batch to 35- 40 C. for pump-out. Batch size of ester will be approximately 12,600 lbs.

Pump to lead-lined sultator and cool to 15 C. 6,300 lbs. of the mono-oleate ester.

-With agitation, add slowly, maintaining temperature of the batch at 15-20 0, 2,520 lbs. 98% fuming sulfuric acid with 20% free sulfur trioxide.

When the sulfuric acid is all added to the mono-ester, allow to stir at 15-20 C. until the titration of a gm. sample is 4555 ml. 0.5 N NaOH to a methyl orange end-point.

Meanwhile, charge to a lead-lined wash tank approximately 1,100 lbs. water and 2,400 lbs. 24% sodium hydroxide.

When the sulfated ester is in specification, add to sodium hydroxide solution with agitation, keeping the temperature below 80 C.

Adjust batch to a titration of 1.0 ml. 0.5 N Hcl per 10 gm. sample to methyl orange.

Turn off stirrer and let batch separate at -80 C. until two clear layers are obtained.

Drain the bottom layer to the sewer (sodium sulfate solution).

Turn on stirrer and blend material in kettle until uniform, While cooling to 40 C.

Adjust batch to 59-61% Water and 05-06% total alkalinity.

It is understood that the above disclosure is intended to include all functional equivalents thereof for compounds and processes which would be obvious to a person of ordinary skill from the above disclosure, and that the invention disclosed herein is limited only to the extent of the appended claim,

I claim:

1. A process for treating textiles to obtain softness and rewettability, said process being compatible with the presence of metallic ions, comprising applying from about 0.25 to 2.0% by weight of fabric of the sodium salt of a sulfated mono-oleate ester of diethylene glycol to said textile, said salt being applied in the form of an aqueous solution.

References Cited UNITED STATES PATENTS 1,936,265 11/1933 Rheiner et al 260400 1,970,578 8/1934 Schoeller et al. 260400 XR 2,079,108 5/ 1937 Dreyfus.

2,129,896 9/ 1938 Whiteman 260-400 2,136,379 11/1938 Flett 260400 2,379,703 7/ 1945 Geltner 260400 MAYER WEINBLATT, Primary Examiner D. L. ALBRECHT, Assistant Examiner.

US. Cl. X.R. 

